#------------------------------------------------------------------------------
#$Date: 2016-03-25 12:15:32 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179806 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/02/7010267.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7010267
loop_
_publ_author_name
'Tulloch, Arran A. D.'
'Danopoulos, Andreas A.'
'Winston, Scott'
'Kleinhenz, Sven'
'Eastham, Graham'
_publ_section_title
;
 N-Functionalised heterocyclic carbene complexes of silver
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              4499
_journal_paper_doi               10.1039/b007504n
_journal_year                    2000
_chemical_formula_moiety         'C34 H50 Ag1 Br0.65 Cl7.35 N4 O2'
_chemical_formula_sum            'C18 H25 Ag Br0.08 Cl0.92 N3 O'
_chemical_formula_weight         446.34
_chemical_name_common            00skl035
_chemical_name_systematic
;
3-mesityl-1-(N,N-diethylacetamido) imidazol-2-ylidene 
silver bromide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.9000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.5398(2)
_cell_length_b                   10.44890(10)
_cell_length_c                   16.8853(2)
_cell_measurement_reflns_used    20698
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     3793.01(8)
_computing_cell_refinement       'Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'Denzo a. Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean '9.091 pixels/mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'π and θ scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21107
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_correction_T_min  0.8205
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SORTAV - multi-scan from symmetry-related measurements (R.H. Blessing, 1995-1997
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1820
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.858
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0912P)²+12.1639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                4535
_reflns_number_total             5526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b007504n.txt
_cod_data_source_block           9b
_cod_original_cell_volume        3793.01(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7010267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.081475(13) 0.62725(3) 0.28795(2) 0.03656(13) Uani 1 1 d . . .
O O 0.15358(12) 0.7639(3) 0.1100(2) 0.0373(6) Uani 1 1 d . . .
Br1 Br 0.04467(4) 0.65670(12) 0.38760(7) 0.0479(4) Uani 0.081(4) 1 d P . .
Cl2 Cl 0.04467(4) 0.65670(12) 0.38760(7) 0.0479(4) Uani 0.919(4) 1 d P . .
N1 N 0.12930(14) 0.5441(3) 0.1638(2) 0.0309(6) Uani 1 1 d . . .
N2 N 0.19475(14) 0.4997(3) 0.3147(2) 0.0321(6) Uani 1 1 d . . .
C2 C 0.22977(18) 0.5056(4) 0.4194(3) 0.0342(8) Uani 1 1 d . . .
C3 C 0.07861(17) 0.6032(4) 0.0740(3) 0.0354(8) Uani 1 1 d . . .
H3A H 0.0437 0.6206 0.0784 0.043 Uiso 1 1 calc R . .
H3B H 0.0636 0.5439 0.0186 0.043 Uiso 1 1 calc R . .
C5 C 0.21650(18) 0.4417(4) 0.2662(3) 0.0360(8) Uani 1 1 d . . .
H5 H 0.2533 0.3920 0.2944 0.043 Uiso 1 1 calc R . .
C6 C 0.10016(17) 0.7289(4) 0.0555(3) 0.0371(8) Uani 1 1 d . . .
C7 C 0.2149(2) 0.4233(4) 0.4680(3) 0.0420(9) Uani 1 1 d . . .
C8 C 0.2781(2) 0.5943(4) 0.4682(3) 0.0394(8) Uani 1 1 d . . .
C9 C 0.17492(18) 0.4701(4) 0.1709(3) 0.0376(8) Uani 1 1 d . . .
H9 H 0.1766 0.4441 0.1186 0.045 Uiso 1 1 calc R . .
C11 C 0.3136(2) 0.5964(5) 0.5697(3) 0.0465(10) Uani 1 1 d . . .
H11 H 0.3467 0.6561 0.6048 0.056 Uiso 1 1 calc R . .
C12 C 0.14050(17) 0.5631(3) 0.2516(3) 0.0313(7) Uani 1 1 d . . .
C13 C 0.2523(2) 0.4299(5) 0.5701(3) 0.0493(11) Uani 1 1 d . . .
H13 H 0.2433 0.3751 0.6052 0.059 Uiso 1 1 calc R . .
C14 C 0.3017(2) 0.5130(5) 0.6214(3) 0.0509(12) Uani 1 1 d . . .
C15 C 0.2917(2) 0.6845(4) 0.4139(3) 0.0470(10) Uani 1 1 d . . .
H15A H 0.2619 0.6701 0.3434 0.070 Uiso 1 1 calc R . .
H15B H 0.3340 0.6695 0.4333 0.070 Uiso 1 1 calc R . .
H15C H 0.2881 0.7729 0.4294 0.070 Uiso 1 1 calc R . .
C17 C 0.3427(3) 0.5168(7) 0.7321(4) 0.0716(18) Uani 1 1 d . . .
H17A H 0.3750 0.5820 0.7549 0.107 Uiso 1 1 calc R . .
H17B H 0.3622 0.4330 0.7578 0.107 Uiso 1 1 calc R . .
H17C H 0.3174 0.5381 0.7552 0.107 Uiso 1 1 calc R . .
C18 C 0.1617(2) 0.3308(5) 0.4139(4) 0.0513(11) Uani 1 1 d . . .
H18A H 0.1590 0.2817 0.4608 0.077 Uiso 1 1 calc R . .
H18B H 0.1684 0.2722 0.3756 0.077 Uiso 1 1 calc R . .
H18C H 0.1228 0.3781 0.3700 0.077 Uiso 1 1 calc R . .
N3 N 0.0574(2) 0.7955(7) -0.0232(4) 0.103(3) Uani 1 1 d . . .
C20 C 0.0729(3) 0.9244(12) -0.0429(7) 0.159(6) Uani 1 1 d . . .
H20A H 0.0715 0.9855 0.0006 0.191 Uiso 1 1 calc R . .
H20B H 0.1169 0.9198 -0.0193 0.191 Uiso 1 1 calc R . .
C21 C -0.0239(7) 0.7739(9) -0.0823(8) 0.178(7) Uani 1 1 d . . .
H21A H -0.0345 0.7280 -0.0427 0.214 Uiso 1 1 calc R . .
H21B H -0.0490 0.8527 -0.1118 0.214 Uiso 1 1 calc R . .
C25 C -0.0217(6) 0.7044(6) -0.1407(7) 0.126(4) Uani 1 1 d . . .
H25A H -0.0633 0.6703 -0.1902 0.188 Uiso 1 1 calc R . .
H25B H 0.0072 0.6335 -0.1049 0.188 Uiso 1 1 calc R . .
H25C H -0.0074 0.7552 -0.1728 0.188 Uiso 1 1 calc R . .
C22 C 0.0465(4) 0.9719(12) -0.1179(13) 0.267(12) Uani 1 1 d . . .
H22A H 0.0629 1.0584 -0.1114 0.400 Uiso 1 1 calc R . .
H22B H 0.0022 0.9768 -0.1453 0.400 Uiso 1 1 calc R . .
H22C H 0.0518 0.9212 -0.1614 0.400 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Ag1 Br1 157.27(10) . . ?
C12 Ag1 Cl2 110.26(10) . 6_556 ?
Br1 Ag1 Cl2 90.14(3) . 6_556 ?
C12 Ag1 Br1 110.26(10) . 6_556 ?
Br1 Ag1 Br1 90.14(3) . 6_556 ?
Cl2 Ag1 Br1 0.00(4) 6_556 6_556 ?
Ag1 Br1 Ag1 88.31(3) . 6_556 ?
C12 N1 C9 111.7(3) . . ?
C12 N1 C3 124.1(3) . . ?
C9 N1 C3 124.0(3) . . ?
C12 N2 C5 111.5(3) . . ?
C12 N2 C2 124.6(3) . . ?
C5 N2 C2 123.5(3) . . ?
C7 C2 C8 122.8(4) . . ?
C7 C2 N2 119.7(4) . . ?
C8 C2 N2 117.5(3) . . ?
N1 C3 C6 110.4(3) . . ?
N1 C3 H3A 109.6 . . ?
C6 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C6 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C9 C5 N2 106.0(3) . . ?
C9 C5 H5 127.0 . . ?
N2 C5 H5 127.0 . . ?
O C6 N3 122.4(4) . . ?
O C6 C3 121.0(3) . . ?
N3 C6 C3 116.7(3) . . ?
C2 C7 C13 117.0(5) . . ?
C2 C7 C18 121.9(4) . . ?
C13 C7 C18 121.0(4) . . ?
C11 C8 C2 117.5(4) . . ?
C11 C8 C15 120.9(4) . . ?
C2 C8 C15 121.6(4) . . ?
C5 C9 N1 106.9(3) . . ?
C5 C9 H9 126.5 . . ?
N1 C9 H9 126.5 . . ?
C8 C11 C14 121.6(5) . . ?
C8 C11 H11 119.2 . . ?
C14 C11 H11 119.2 . . ?
N1 C12 N2 103.9(3) . . ?
N1 C12 Ag1 130.5(3) . . ?
N2 C12 Ag1 123.7(2) . . ?
C14 C13 C7 122.1(4) . . ?
C14 C13 H13 118.9 . . ?
C7 C13 H13 118.9 . . ?
C13 C14 C11 118.9(4) . . ?
C13 C14 C17 121.5(5) . . ?
C11 C14 C17 119.5(5) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 N3 C20 120.4(4) . . ?
C6 N3 C21 122.5(4) . . ?
C20 N3 C21 112.8(5) . . ?
C22 C20 N3 124.5(9) . . ?
C22 C20 H20A 106.2 . . ?
N3 C20 H20A 106.2 . . ?
C22 C20 H20B 106.2 . . ?
N3 C20 H20B 106.2 . . ?
H20A C20 H20B 106.4 . . ?
C25 C21 N3 85.1(9) . . ?
C25 C21 H21A 114.5 . . ?
N3 C21 H21A 114.5 . . ?
C25 C21 H21B 114.5 . . ?
N3 C21 H21B 114.5 . . ?
H21A C21 H21B 111.6 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 C12 2.099(3) . ?
Ag1 Br1 2.4099(9) . ?
Ag1 Cl2 2.9071(10) 6_556 ?
Ag1 Br1 2.9071(10) 6_556 ?
O C6 1.208(4) . ?
Br1 Ag1 2.9071(10) 6_556 ?
N1 C12 1.346(4) . ?
N1 C9 1.381(5) . ?
N1 C3 1.448(5) . ?
N2 C12 1.359(5) . ?
N2 C5 1.389(4) . ?
N2 C2 1.438(5) . ?
C2 C7 1.394(5) . ?
C2 C8 1.395(6) . ?
C3 C6 1.536(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C9 1.346(6) . ?
C5 H5 0.9500 . ?
C6 N3 1.330(6) . ?
C7 C13 1.399(6) . ?
C7 C18 1.501(7) . ?
C8 C11 1.390(6) . ?
C8 C15 1.499(6) . ?
C9 H9 0.9500 . ?
C11 C14 1.393(7) . ?
C11 H11 0.9500 . ?
C13 C14 1.375(8) . ?
C13 H13 0.9500 . ?
C14 C17 1.515(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N3 C20 1.502(9) . ?
N3 C21 1.783(16) . ?
C20 C22 1.140(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C25 1.254(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 Ag1 Br1 Ag1 -142.4(3) . . . 6_556 ?
Cl2 Ag1 Br1 Ag1 12.06(5) 6_556 . . 6_556 ?
Br1 Ag1 Br1 Ag1 12.06(5) 6_556 . . 6_556 ?
C12 N2 C2 C7 85.6(5) . . . . ?
C5 N2 C2 C7 -103.0(4) . . . . ?
C12 N2 C2 C8 -94.9(4) . . . . ?
C5 N2 C2 C8 76.5(5) . . . . ?
C12 N1 C3 C6 92.6(4) . . . . ?
C9 N1 C3 C6 -81.9(4) . . . . ?
C12 N2 C5 C9 0.2(4) . . . . ?
C2 N2 C5 C9 -172.2(4) . . . . ?
N1 C3 C6 O 2.7(5) . . . . ?
N1 C3 C6 N3 -177.7(5) . . . . ?
C8 C2 C7 C13 -2.1(5) . . . . ?
N2 C2 C7 C13 177.4(3) . . . . ?
C8 C2 C7 C18 178.4(4) . . . . ?
N2 C2 C7 C18 -2.1(5) . . . . ?
C7 C2 C8 C11 2.0(6) . . . . ?
N2 C2 C8 C11 -177.5(3) . . . . ?
C7 C2 C8 C15 -178.0(4) . . . . ?
N2 C2 C8 C15 2.6(5) . . . . ?
N2 C5 C9 N1 0.1(4) . . . . ?
C12 N1 C9 C5 -0.3(4) . . . . ?
C3 N1 C9 C5 174.7(3) . . . . ?
C2 C8 C11 C14 0.2(6) . . . . ?
C15 C8 C11 C14 -179.9(4) . . . . ?
C9 N1 C12 N2 0.4(4) . . . . ?
C3 N1 C12 N2 -174.6(3) . . . . ?
C9 N1 C12 Ag1 -163.9(3) . . . . ?
C3 N1 C12 Ag1 21.1(5) . . . . ?
C5 N2 C12 N1 -0.4(4) . . . . ?
C2 N2 C12 N1 171.9(3) . . . . ?
C5 N2 C12 Ag1 165.3(3) . . . . ?
C2 N2 C12 Ag1 -22.4(5) . . . . ?
Br1 Ag1 C12 N1 157.7(2) . . . . ?
Cl2 Ag1 C12 N1 5.1(4) 6_556 . . . ?
Br1 Ag1 C12 N1 5.1(4) 6_556 . . . ?
Br1 Ag1 C12 N2 -4.0(5) . . . . ?
Cl2 Ag1 C12 N2 -156.6(3) 6_556 . . . ?
Br1 Ag1 C12 N2 -156.6(3) 6_556 . . . ?
C2 C7 C13 C14 -0.1(6) . . . . ?
C18 C7 C13 C14 179.4(4) . . . . ?
C7 C13 C14 C11 2.1(6) . . . . ?
C7 C13 C14 C17 -178.6(4) . . . . ?
C8 C11 C14 C13 -2.2(6) . . . . ?
C8 C11 C14 C17 178.5(4) . . . . ?
O C6 N3 C20 -5.3(12) . . . . ?
C3 C6 N3 C20 175.2(9) . . . . ?
O C6 N3 C21 -160.4(6) . . . . ?
C3 C6 N3 C21 20.0(9) . . . . ?
C6 N3 C20 C22 158.0(18) . . . . ?
C21 N3 C20 C22 -45(2) . . . . ?
C6 N3 C21 C25 -98.4(8) . . . . ?
C20 N3 C21 C25 104.7(9) . . . . ?
